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Red Auerbach’s last victory cigar as Celtics coach squares off against Mike Milbury beating a Ranger fan with a shoe in the first round of Boston’s Greatest Sports Moment tournament.

1. Red Auerbach’s final victory cigar in 1966One thing is certain about the late, great Red Auerbach: He loved cigars, particularly when they followed a victory. He was frequently seen lighting them up after wins during his tenure as Celtics head coach, which featured nine NBA championships. After a championship-clinching 95-93 win over the Lakers in the 1966 NBA Finals, Celtics fans everywhere witnessed a touching moment when Auerbach lit up his last victory cigar as the team’s head coach. The championship was the eighth consecutive for the C’s, and the ninth in 10 years. The great Bill Russell, who replaced Auerbach as Boston’s coach the following season, finished the game with 25 points and a spectacular 32 rebounds. Auerbach moved to the front office after his coaching days. And it’s hard to picture Red without also picturing the trademark victory stogie hanging out of his mouth.

16. Mike Milbury beats Rangers fan with shoeThis candidate for Boston’s Greatest Sports Moment could also be a candidate for Boston’s Strangest Sports Moment. Bruins defenseman and Massachusetts native Mike Milbury made Bruins fans proud and Rangers fans angry on Dec. 23, 1979, in a game at Madison Square Garden. After a fight broke out between Boston’s Al Secord and New York’s Ulf Nilsson, Rangers fan John Kaptain did the unthinkable and smacked the Bruins’ Stan Jonathan with a rolled-up program. The Bruins then took the fight into the stands, and Kaptain got a taste of his own medicine, as Milbury proceeded to beat him with his own shoe. The altercation will not be part of any NHL marketing seminar on how to create a family-friendly game experience, but the incident defined the no-nonsense, lunch-pail attitude of the Big Bad Bruins of the 1970s and ’80s.